


The Initiation of Dean Winchester: The Pink Panties of Rhonda Hurley

by SpankedbySpike



Category: Supernatural
Genre: Crossdressing, F/M, First Time, Mutual Masturbation, Pink Panties, Teenagers, Underage - Freeform
Language: English
Status: Completed
Published: 2012-02-17
Updated: 2012-02-17
Packaged: 2017-10-31 08:02:45
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,992
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/341797
Author URL: https://archiveofourown.org/users/SpankedbySpike/pseuds/SpankedbySpike
Summary: <blockquote class="userstuff">
              <p>A story dedicated to Smut_Slut, written for her Birthday (I know, I am a little late… Sorry!), I hope you will enjoy this personal vision of how this particular back-story played out.</p>
<p>The story is inspired by the following comment made by Dean to his alter-ego of the future: "…being in her panties is the best next thing to being in her pussy…"</p>
            </blockquote>





	The Initiation of Dean Winchester: The Pink Panties of Rhonda Hurley

**Author's Note:**

  * For [smut_slut](https://archiveofourown.org/gifts?recipient=smut_slut).



> This fantasy is what could have made both Future Dean and our Dean dream for years…

The Initiation of Dean Winchester: The Pink Panties of Rhonda Hurley, Spanked by Spike

 

Dean was restless. John had left the boys last night and the Saturday has been spent helping Sammy, feeding him, driving him around, answering his questions, entertaining him. Rhonda Hurley had hinted all week long that she was more than interested in some action and he was eager to make it happen. The girl was a dream come true: the look of a pinup, the dirty mind of a teenager, the fantasy of most guys in the school and of a few girls too!

 

 

The evening couldn’t come early enough. Sam was settled for a night of watching a rented movie; he was set to visit Rhonda at dinnertime when her parents would be away at a restaurant celebrating something or another. He took a long shower, reducing the stress of the day, slapping on enough of Pa Winchester’s aftershave to last him for the night. It took a longer time to get dressed, well enough to impress, easy enough to undress when the time came to turn on the charm. She wouldn’t be his first girl but she definitively would make the stay in this Podunk town agreeable, pleasurable even, who was he kidding? Enthralling, probably…

 

The opportunity was just too good to pass and he’d been fantasizing about it all week. Still, nothing could prepare him for the surprise he really got. He rang the bell to the small suburban house, waiting patiently in the calm of the twilight, no neighbor paying attention to him; he was relaxed and smooth, until the door opened. Rhonda saluted him with a wink, standing with a hand laid high on the doorframe. Wearing the tiniest and brightest piece of red lingerie Dean had ever seen in his life, Rhonda lounged against the frame of the door, providing him with a snapshot that would last him a lifetime. A barely dressed nymph, inviting him in… There was a God! And he was looking out for him!

 

Desire flared and overcame any thinking brain cells he may have possessed. The daydreams he lived on that gave him enough sustenance between trips and moves were now being reachable and his hand shot straight to follow the curve of a wonderfully displayed breast. He pushed past the door and caged the dream vision against the wall, licking a path towards the perky and full heaven waiting for him. She had enough sense to close the door and pull her hands around the stud at hand, caressing the nape of his neck and the large shoulders holding her in place.

 

Finally able to suck a covered nipple, Dean calmed down enough to push up and look at Rhonda smoky eyes. “Babe, you know how to host a party!” he whispered before finally kissing her.

 

The kiss started with butterfly touches on the side of her lips, her nose, her closing eyelids before coming back to the swollen lips and pushing forward, breaching the soft barrier created by the small teeth and fully conquering the warm mouth opening on a sigh. Blissful wasn’t starting to define the state the young Winchester was in, the lovely girl in his arms enjoying herself about as much.

 

His hands couldn’t stay still, roaming on the writhing body pinned by the door, reveling in the soft and satiny structure of the two garment pieces barely covering Rhonda. Just to thank her he was willing to give her the moon. Heck, no punishment that his dad could dole out would tame the reality of the fun he was going to have tonight.

He finally stood away, letting his eyes commit to memory the delicious curves on display.

 

“Oh, Rhonda… Damn, you made my day!” He was almost panting.

 

She smiled and changed the pose, directing his gaze to the crotch pulling the lines of the red panty covering the Valhalla.

 

“Girl, you are smoking tonight! C’me here…” and he beckoned to the fellow student while he backed himself on the sofa furnishing the seating room. He didn’t sit as much as fall in it, spreading his legs and holding his arm out in invitation. “Will we? Tonight?” he whispered to the babe sitting on his lap.

 

“Maybe... Will you do something for me first?” she replied.

 

“Just ask, I am all yours tonight.” He invited with a roguish smile.

 

‘Well, I’ve been curious about something for awhile and there is no way, I’d ever ask any of the guys in town…” she let the sentence falter, looking at her hands instead of facing his expectant gaze.

 

“You can tell me. I’m the new guy here; there is no one I’d talked to about anything you want to share with me. Rhonda?” and with determined fingers he moved her face up so he could ascertain her real intent.

 

“It’s a little odd. You gonna think I am a freak.” And now she settled herself against his flannel-covered shirt instead, the eyes closed, trying to find the courage to breach the subject of her fantasies.

 

“Try me, babe. I doubt anything you can do or say will creep me out.” He answered resolutely.

 

“I’d really like to see a guy in underwear, not just fondle someone in the dark of a movie theatre…” she whispered in the crook of his neck.

 

“That’s it? It won’t be as pretty as your get up, I can tell you that right now…” he said with a rumbling laugh.

 

“Yes, but I want to look at you and have you try stuff…” she added, looking at him with doe eyes.

 

Dean failed to see the problem. He’d get to parade in his underwear or model for a girl already halfway there, that much closer to get in her panties. Oh man, all good in his book!

 

“Anyway you want me, baby. Tonight I am all yours!” he assured her with a luminous smile. Gee, how horny was he? His cock had filled when he saw the beautiful teenager at the door, but now with all this talk and the almost certainty of passing second base made it hard as steel. He’d never been so uncomfortable and yet that pain was the sweetest he’d ever experienced. The jeans were way too tight now and his breathing slightly irregular, yet, he couldn’t stop touching the delicate skin offered to his questing fingers. His hands had a life of their own. One holding the small waist of the girl on his lap, the other roaming between the swell of the firm breast crushed against his clothed torso and the flat tummy fluttering under his caresses. Cloud nine was just down this path… he started hyperventilating.

 

Rhonda moved with his touches, smiling at the prospect presented by this evening and the young rebel holding her so tight. She turned into the embrace and kissed him, like the starved hormonal girl she was, with complete abandon. Her small hands started working on the few buttons of the shirt left to open, flattening her palms on the defined pectorals outlined by the tight t-shirt underneath. Smooth and firm, her libido revved just imagining that body undressed and adorned only by the most feminine of underwear; A dark and forbidden fantasy, finally available to build upon in the long lonely nights to come.

 

The kiss lasted for an eternity, a long filled minute. They broke apart breathless, ready to move this party to the next level. Rhonda rose gracefully and offered her hand to Dean. He did not let her wait, eager to enjoy the backside view of this sexy young woman.

 

The bedroom door was soon enough closed behind them and while she settled against the headboard of the full bed occupying the center of the room, he discarded his shirt on the small desk close by, pulling the black t-shirt over his head, displaying the corded muscles of his upper body with the full movement. She was enthralled and let a hand slightly trace the beaded peak of a needy and still covered nipple. The progress of her hand was slow and hypnotic, Dean unbuckled without even realizing what he was doing, all his focus on the tantalizing breast underlined by the gesture. The zipper opening was loud in a room where the only sound so far was the muted breathing of the two teenagers. A small amount of relief reached the dizzy brain of Dean once the pressure on his dick was partially relieved. His opened jeans fell lower on his hips, displaying the soft cotton briefs tenting underneath. Rhonda’s hitch was quiet and accompanied by the lowering of her other hand to her pussy, fingers pushing the slippery fabric of her red and silky panties inside her wet core. Dean moaned and pushed the pants down, unceremoniously kicking the basketball shoes and legs out of the way; His own hand flying to cup his turgid erection, palmed by the cotton but twitching with a mind of its own.

 

Her tongue stroked out and outlined the red lips that were previously forming such a straight line in her eagerness to keep her pleasure hidden but now her whole body was calling out to the young Winchester.

 

Oh, shit! Dean was a goner! He slowly walked to the bed and let his hand caress the stretched leg, slightly opening to the treasure he needed to explore and conquer. Her skin was so satiny, he could spend hours just touching the young girl, reaching the back of her knee, he watched with awe the expressive shiver that ran through her, quite disposed to discover more of those special spots, wanting to make it awesome for her, finally happy to have the time and the girl ready to let him do some serious investigating. His balls started to ache; Dean simply did not know if he should be praying to last or to just get it over quickly first, so he could concentrate on better things later that evening. She moaned and that astonishing sound brought his gaze to the flushed face devouring him. He felt self-conscious for a moment before realizing how positive her appraisal of his trim body really was. His fingers had a death grip on the base of his cotton encased cock, yet it still enlarged following the lead of his teenage brain cells firing up like a volcano.

 

“Dean… Kiss me.” She barely finished breathing the request before he was already complying, covering the full lips, tilting his head, reaching out inside and tickling the gum recesses until she squirmed. He felt compelled to let his grip slide and cover her hand at the juncture of her thighs. His longer fingers brushed over her small palm, trying to add pressure to whatever she was doing. With a cry, she removed her finger from her insides, and Dean, without looking, patted the covered pussy before lifting one side and inserting his middle finger through the wet lips opening for him. It was too little and too much, his palm started applying pressure around the still hidden clit, while his thumb was going up and down, following the entrance he so wanted to breach. Establishing a rhythm that seemed to make her happy, he trailed a new path along her feminine jaw line with his mouth, reaching the sensitive spot behind her left ears, licking and sucking and she suddenly shot like a firecracker, her back bowing, her legs closing on his hand, her inner muscles fluttering and rippling underneath his strong hand. He could have come if only he was in a better position. He breathed out the demands made by his combusting body and smiled at the contented girl on the bed.

 

“Oh boy! Oh my!” Rhonda didn’t have it in her to complete a full thought or sentence yet, so instead she gripped the hand still covering her and brought it to her mouth, kissing the open palm, sucking the pads of the fingers she could put in her mouth, smiling through it all and watching him intently all along.

 

Dean was ready to shuck their sets of underwear, he definitively needed some skin on skin action, but she tut tutted him and with her hand directed him to stand. He left her side and stood about five feet from the bed. With a coy grin she asked him if he was still up to keeping his earlier promise. Horny as he was, he noted slowly.

 

“Can you turn for me Dean?” The boy did, sneaking a quick hand in to tuck himself better and hide the head of his cock peaking at his waistband. By the time he faced her again, she was seated rather than lounging and had a look of rapture on her face that he wasn’t sure how to interpret. He’s seen himself in a mirror before, not that impressed. His father was better built, his brother was getting taller, he could see his muscles and the smooth expanse of skin was well tanned but just didn’t get the especially fascinated look she was sporting. He stood taller, sucking air just to make his 6 pack more prominent and smiled.

 

“Will you fondle yourself, show me what you like?” Dean dropped one hand on his cock, the other cupped his sac. She couldn’t really see what he was doing, on account that he was still covered but the movements were erotic, the tension on his body palpable and the speed he was gaining a dead giveaway on the lack of time she had to see things her way.

 

“Stop!” he couldn’t hear anymore and was speeding away.

 

“Dean, stop!” he paused only because he remembered he could score, pinning his jerking cock against himself.

 

Rhonda scooted off the bed and leaned towards the night table, pushing things around and coming out with something brilliant and satiny bunched in her hand. Dean shuddered, interested and not being able to hide the leaking precum staining his underwear. She stood and ran her hands on him, stopping at a hard male nipple to nick, sucking at the throbbing vein in his neck, fully falling in his embrace and feeling the response of his teenage body on the tight muscles of her midriff for added incentive, and the boy was begging her for action.

 

“Can I undress you Dean?”

 

“Mmmhm”

 

On her knees, pulling the briefs down, she was gorgeous. He stepped out of them, closing his eyes, quite aware of the fact he couldn’t hide his excitement anymore, not paying attention to the fact that she was dressing him up with something else. He felt her lower herself towards his crotch but the expected feel of her tongue wasn’t what he imagined. He opened his eyes to find Rhonda smoothing pink panties on him. He was too surprised to utter a word but flinched enough that she quickly cooed him with small whispers.

 

“It’s okay… You promised…”

 

Dean looked down, surprised to acknowledge how soft the garment was on his over sensitized member. The fit was a little tight but also quite supportive of his package. Even the moisture spreading over the panty felt good rather than upsetting. Still, he did not think he should enjoy it, yet, once Rhonda’s tongue swept the outlined cock through the cloth, he cried out. It was good. She mouthed the twitching head and he felt his knees buckle. Her nimble fingers were massaging his balls and his cock was fighting a losing battle for not coming out of the constrictive article of clothing. Her mouth never left things to chance though. He was completely under her charm, not daring to move not knowing how to stop. Her hands had to hold his thighs, rubbing his clenched buttocks, while her tongue was focusing on his prick in the most amazing way.

 

Dean had never felt anything like this. The softness surrounding his dick was simply impossible to describe, the whole front of the feminine underwear covering him was now wet, bunched at places, stretched by the heavy package beneath. His mind was reeling, enjoying the attention lavished on him so much he knew he’d come soon.

 

“Rhonda, I’m…”

 

“Shsh… I know… Come on Dean, let go.”

 

And just like that, he did. The tension left his spine, his legs locked and his hands flew to her head. He exhorted her with grunts and half-worded pleas, she continued her ministrations nevertheless. His shallow thrusts became more urgent and the energy expanded sizzled between them, all sense of rhythm lost, both minds focusing on the finish line and reaching it in an erratic way, the orgasm swapping any remaining strength, Dean collapsed on the floor, kneeling in front of Rhonda, searching her mouth like a starved man.

 

That kiss was messy, a perfect counterpoint to the sticky pink satin panties stretching over him and molding his softening penis. Her little hands went around the teenager’s back holding him to her and together they managed to get to the bed and cuddle. They knew they were running out of time but just couldn’t seem to function at full speed. Finally, Rhonda rose to her knees and started withdrawing the stained panties from Dean and followed the gesture with small kisses and licks. The pressure applied was light enough that it was pleasant, but not exciting, and soon after, he was back in his own briefs lovingly put back by the girl.

 

He managed to stand on his two feet and finish dressing before kissing her goodbye, testing remnants of himself for the first time in his young life. The ushered promise of meeting again the following week-end were made and he sadly left her room, keeping in mind a picture of Rhonda Hurley shedding her own bra and panties and slipping inside the covers of her bed. He just could not wait for next Saturday!

 

 

The end.

 

_Hope you had some fun Smut_Slut..._

**Author's Note:**

> Crossposted at my LJ http://spankedbyspike.livejournal.com/4258.html


End file.
